Google already has plenty of articles on how to get into Cuba as an American citizen. Long story short – it used to be really easy, now it’s just pretty easy. I went in 2016 under the “People to People” category, which has since been removed as an option. That doesn’t mean you can’t go. You definitely can and you definitely should.
Cuba is a world of contradictions. The streets of Havana are covered in trash, the homes are run down and the population is poor; yet there is no crime. Not one person spoke highly of the Castro regime, yet they all genuinely mourned Fidel’s death for a week. The people are incredibly warm, talkative and inviting, yet they swindle you out of your money at every opportunity.
Our first mission was to figure out how the hell it all worked. Under a communist regime, how do people feed and shelter themselves? What is permitted and what isn’t? How do the health care, education and economic systems work?
We never really got a full answer, but one thing is for sure, money still dictates life and those with more of it have nicer houses and live in better neighborhoods. We heard that tax rates are about 90%, and a doctor might take home about $40 per month after taxes, while someone in the service industry will take home about $25. That can make a difference, but not nearly the income inequality we see in the states. Oddly, we stayed with a French Canadian woman who had somehow found a way to buy a house in Trinidad (a town in Cuba) and claimed that her tax rate was 10%. Who knows.
All that being said, the beauty of the island and friendliness of the people made the trip unforgettable. Each day we’d wake up and have only the loosest itinerary, ready for whatever adventure might come our way. Being back, I have a new appreciation for life not dictated smart phones or even precise timing.
Havana is a quick three hour flight from New York. It was all painless except for the fact that I thought I would beat the system by taking out Euros at the airport instead of dollars to avoid the 10% penalty on American dollars in Cuba, but got such a bad exchange rate, that it actually cost me more. Whoops.
Pro Tip: Order Euros from you bank ahead of time.
We arrived at Rolando’s hostel at around 3 PM and after a few minutes to get settled, met with Enrique, who ran the place, so he could explain the house rules and the essentials for getting around Cuba.
Cuba runs on a two currency system. Local Pesos, or CUP, at 25-1 to the dollar are used to buy small items; Convertible Pesos, or CUC, are basically 1-1 with the dollar and can buy everything. We were instructed to take out almost entirely CUC, but some CUP because we’ll be able to buy some food for cheaper.
It was a disaster at the bank. I’m still learning Spanish and the teller understood my request as “50 CUC worth of CUP,” instead of “50 total of CUP.” I got a FAT STACK of CUP, which I couldn’t spend in a lifetime, and eventually begged enough to get it all in CUC. Don’t do that. If you can’t speak Spanish fluently, it is probably easiest to just write it down.
We left the bank and headed towards Old Havana, which is significantly nicer (and more expensive and touristy) than Central Havana, where we were staying. It’s also, the only place to get food other than cheap ham and cheese sandwiches.
When you visit, find a good spot in one of the many bars with live salsa music and get some food. The food in Cuba overall isn’t anything special, so just stick to the classics like Ropa Vieja, Arroz con Pollo or Lomo de Cerdo.
At the bar, we were approached by a super friendly guy who claimed to be a retired boxer, but, turned out, was a pimp. Prostitution is pretty rampant in Havana, but it’s really not an issue, just decline respectfully and all is good.
Day two was raining. We had heard that there were free walking tours starting in Old Havana, but since we couldn’t find them, we decided it was worth $20 to pay for a walking + bus tour. It really was, because we got a chance to ask direct questions to a Cuban about how the country works. She really formed the base of our knowledge of the economy and social structure.
The bus toured all around Havana, including going across the river to the fort overlooking the city. We were lucky enough to have the rain stop at this point and it was an absolutely beautiful view. We also saw the more wealthy neighborhoods in the western part of Havana. These nice homes were originally given to the maids and other workers after the revolution, but at this point, it seems that those with better jobs and more money have purchased them and live there again (mostly government employees and diplomats).
We also went to the National Art Museum on a recommendation and were disappointed. It wasn’t Cuban, it was mostly artifacts from ancient Egypt, Greece, Rome and China, and nothing particularly interesting of any of those.
One note about internet. The only place in the whole city (including hostels and private residences) to get WiFi access is in designated parks. Personally, I like to unplug while I’m on vacation, but there are some real logistical challenges to having limited internet access. Something to keep in mind.
That night, we bounced around Central Havana until we ended up at a bar that was quite the melting pot. It had plenty of locals, German tourists, a Cuban couple from Miami who were decked out head to toe in American Flag gear, and a dude who had just opened up a restaurant in the West Village.
On day three the sun came out in a big way. It was a beautiful day (as was every day for the rest of the trip). We decided to go wandering with some people we met at the hostel.
We had pork hamburgers and smoked cigars at a brewery in Plaza Viejo. It was great to take our time and not have any particular agenda. We wandered around from there to the Malecon, which is the promenade that separates the water from the city. When it was raining the previous day, the water was crashing into the sea wall and spilling over, but on this day is was as calm as could be.
We decided it would be fun to rent one of the old cars that are everywhere and joy ride up and down the Malecon with the roof down. It was a blast.
Note – you do not need to book this in advance, there are plenty of opportunistic to rent them at any time.
Afterwards, I went back to the hostel because I had made plans to play basketball with one of the bartenders at the hostel. I didn’t have the right shoes and my Spanish was really rough, but sports can be the only language you need sometimes. It was a great way to get to know Cubans outside of the server-tourist relationship.
A note on Cuban friendliness. It’s common to hear Americans say that the locals are friendly in many places. Cubans set the bar. A couple at the hostel were walking down the street one day and made a innocuous passing remark like “excuse me” to a few Cubans. This was enough for the Cubans to start a conversation and pretty quickly invite the couple over to their home. Turned out the Cubans were artists and were literally building an internal wall in their home. They fed the couple and pumped them full of local rum and together they went to work on building this wall. As crazy as that sounds, it’s just another day in Havana.
Anyway, that night, we made sure to go to Fabrica early, and got in after a wait in the line. It was quite the experience. First off, it is a huge venue. There were paintings and other art installations everywhere. There were also a wide variety of music acts, including jazz and a Cuban death metal band.
As the night was winding down, we met some hilariously drunk Mexicans that spoke Spanish so quickly that it sounded like a machine gun. Still, we could decipher enough to have a blast with them until about 5 in the morning.
Early in the morning on Monday, five of us from the hostel jumped into a taxi collectivo to head west to Viñales. We had originally planned to head east and spend two days at the Varadero beach, but got persuaded to go to Viñales instead. This was 100% the right move. Varadero is just a touristy beach town that you could get anywhere in the Caribbean. If you’re going to be in Cuba, you might as well experience the uniqueness of it all.
A note on taxi collectivos. These are basically low-tech Ubers for getting between cities. Your host can book you a taxi collectivo anytime by calling their network. You may be sharing with others, but you do get to experience riding in a car from the 1950’s (though not as well maintained as the ones you can rent in Havana – AC should not be expected).
Viñales is a small town in western Cuba that is growing rapidly thanks to its famous horses, cigar plantations and scenery. It really was beautiful. The streets are dirt for the most part and there are chickens, dogs and horses walking aimlessly around the town. Most houses have porches and it is normal to sit on the porch and strike up conversations with passerbys, or to wander yourself and talk to people on their porches.
After settling in and getting some lunch, we took a taxi up to hotel Horizontes La Ermita, which overlooks the city. They had a swimming pool and it was such a pleasant evening.
We woke up early, had breakfast and took a taxi to a local farm. We arrived and were assigned horses to ride on throughout the farm.
A note on booking accommodations and tours. Nothing we did was booked or planned ahead of time. Airbnb totally exists and you’re welcome to use it, but I liked using the local system. Basically, you can book at Casa Particular at anytime by telling your current host where you’re going. They’ll call their friends in the next place and find you a place to stay as well as a Collectivo to get there. While staying there, they can book you local tours and excursions at any time. So, as long as you know where you’re staying your first night in Cuba, you should be all set.
Our first stop during the tour was at the rum producing part of the farm. We got to try two types of rum: one that was similar to the rum that we always drink, and one that was a little less alcoholic and way sweeter (it kind of tasted like Amaretto). Afterwards, we got back on our horses and headed to the tobacco and cigar making section. We learned about the different parts of the plant and how they are used to make the different cigar brands.
Next, we got to a set of caves with a separate tour by a funny little Cuban tour guide. He told me to watch my head in the cave because I’m tall and then told my friend Jamin to watch out too because… and he made the gesture of horns with his fingers. I’m sure he makes this joke all the time, but I exploded in laughter because Jamin was the only Jewish person on the tour and it seemed like he was saying to watch out for his Jew Horns. No body else got it, including the tour guide.
The caves were cool. Some of the rocks could be played like drums and there were some very interesting shapes. Afterwards, we got a chance to go swimming in a lake nearby. It was a blazing hot day, so this was a great relief. We finished the tour getting an explanation of exactly how cigars are rolled. This was really interesting and we got to smoke cigars dipped in honey afterwards.
After some pictures, we headed home and decided to walk back up to the hotel on the hill. This was funny, because we got terrible explanations from our host and ended up in a farmer’s backyard. The farmer started telling us the route from back where we came, but changed his mind and brought us across his farm for a “shortcut.” This shortcut was more direct, but included dodging some bulls tied to stakes, jumping across a stream, ducking under barbed wire and walking across another farmer’s land. Eventually, we made it up and had another nice night.
We got up early and got into another taxi collectivo to go all the way east, past Havana to our next stop, Trinidad. This trip took about 8 hours.
When we arrived in Trinidad, we found our host, who was a French Canadian woman who had been traveling to Cuba for 30 years, and finally decided to settle down. She was super interesting and clearly loved her life there. She had some beautiful birds and loved to drink. “Porque No?” was our favorite phrase to each other.
Trinidad is a very old town, settled by Spaniards in the 1500’s and still pretty much exclusively cobblestone streets. There is no grid and it is incredibly easy to get lost. We went out our first night to the Casa De La Musica, which had really impressive live Salsa.
The next day, we rented bikes and rode them out of town, down the coast and to the beach. The bike ride was about 6 miles on very rickety bikes, which killed my butt, but it was totally worth it. Such an incredibly beautiful ride.
We had a great day at the beach, including smoking cigars and drinking Piña Coladas. The sun was so gentle, at no point did it feel like it was burning my skin (this was December). The water was perfect too; a nice, cool relief from the beach, but not too cold to make it difficult to be in or out.
The bike ride back was brutal, but we eventually made it. A Cuban sea shell salesman caught our drift, so we had some company. That night, after resting, we made our way to The Disco Ayala, a club a little outside of town that went down into an enormously cavernous space.
In the morning, I went to Cienfuegos. We got in, and went as quickly as possible to the beach. There were no bikes this time, we took a taxi. The beach was super quiet and there were very few people there. We settled down and had a wonderful relaxing time.
Towards the end of the day, two men came out of the ocean holding a bunch of lobsters in their hands. I yelled out “LANGOSTAS!” and the men came over and said I could buy all of the lobsters for $20. I wasn’t about to let that opportunity pass by, so I made the purchase.
The beach attendant was nice enough to put them on ice and we watched the sun set slowly into the water. It was an amazing sight to see.
When our cab came to pick us up I was very excited to tell him that we bought lobsters. He was not happy. This was against the law (the governments technically owns everything, even the lobster in the sea) and there could be severe penalties if we got caught. We put them in the trunk and nothing bad happened. Back at the hostel, I showed them the lobsters and asked if we could use the kitchen, hoping that they would say “No, we’ll cook them for you.” Instead they said “Sure, no problem.”
Somehow I broke open the lobsters by hand and grilled them (that’s how they do it down there). We had them with some rice with pineapple and some wine to go with it.
After dinner we wandered to Parque Jose Marti and found a small outdoor bar tucked into the end of the square. It was super lucky, because the jazz band that started playing was mind blowing. They had a saxophonist, trumpeter, drummer and singer/guitarist. Beers were $1 and it was the perfect end to the day. Cienfuegos has great jazz, make sure to find it during your stay.
We went back to Havana in the morning in a collectivo. Once we got back to Rolando’s we put our stuff down and went to buy presents and visit the revolution museum. I bought my mom a ring for her birthday the next day. I think she likes it because she was wearing it last time I saw her 🙂
The revolution museum was very interesting. They had no problem trying to be politically correct – often calling the United States “Yankee Imperialists.” The museum had a clear agenda to support the revolution and the current regime. It is actually in the old and beautiful presidential palace and I did learn some things.
Fidel Castro seems to have been corrupted by absolute power (as most do), but his personal ambition, bravery and intelligence are admirable. He successfully defended himself in court after a failed revolution and personally lead the guerrilla warfare against the regime and defense of the Bay of Pigs.